Triethylamine → 5-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carbonitrile

HRID 729453노트

반응식

HRID 729453 반응식
[Br:1][C:2]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]([C:17]([NH2:19])=O)=[N:15][CH:16]=2)[CH2:7][CH2:6]1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[Br:1][C:2]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]([C:17]#[N:19])=[N:15][CH:16]=2)[CH2:7][CH2:6]1

참가 물질

4

반응물 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 690622895-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carboxamide

생성물 1

HCID 688192205-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carbonitrile

실험 절차

To a suspension of 5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carboxamide from Step 4 (1.65 g, 4.17 mmol) in TBF (50 mL) at 0° C. was added triethylamine (1.45 mL, 10.5 mmol) followed by trifluoroacetic anhydride (0.885 mL, 6.26 mmol). After a period of 10 min at 0° C., the reaction mixture was raised gradually to room temperature. The mixture was then partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, dried over sodium sulfate and evaporated. The crude mixture was purified by flash chromatography (35% ethyl acetate in hexane) to provide the title compound.

후처리

  1. customThe mixture was then partitioned between ethyl acetate and aqueous sodium bicarbonate
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude mixture was purified by flash chromatography (35% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-928bd42788174a00a6b2e0288675f414
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582633B2

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